After six months of regular and postseason play, the 2016 World Series will see two teams competing, neither of which have experienced a championship in a very long time. The Chicago Cubs will try to break their 108-year curse, and the Cleveland Indians will try to break a curse of their own by becoming the latest city to win two sports championships in the same year (alongside LeBron James’ Cavaliers).

We got a chance to catch up with Filiere after his historic night getting drafted in the eighth round (highest among the three drafted ballplayers from MIT) and asked him about his experiences so far and what he is looking forward to.